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| | 6-Methyleneandrost-4-ene-3,17-dione Basic information |
| Product Name: | 6-Methyleneandrost-4-ene-3,17-dione | | Synonyms: | 6-Methyleneandrost-4-ene-3,7-dione;Androst-4-ene-3,17-dione-6-methylene;Exemestane Related Compound A (15 mg) (6-Methyleneandrosta-4-ene-3,17-dione);1,2-Dihydro ExeMestane;6-Methyleneandrost-4-en-3,17-dione;ExeMestane Related CoMpound A;6-Methylene-4-androstene-3,17-dione;6-Methylene-4-Androsten-3,17-dione | | CAS: | 19457-55-7 | | MF: | C20H26O2 | | MW: | 298.42 | | EINECS: | | | Product Categories: | steroids;API | | Mol File: | 19457-55-7.mol |  |
| | 6-Methyleneandrost-4-ene-3,17-dione Chemical Properties |
| Melting point | 163-165 °C | | Boiling point | 450.8±45.0 °C(Predicted) | | density | 1.11±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | Chloroform (Sparingly), DMSO (Heated), Methanol (Slightly) | | form | Solid | | color | Pale Yellow to Light Beige | | InChI | InChI=1S/C20H26O2/c1-12-10-14-15-4-5-18(22)20(15,3)9-7-16(14)19(2)8-6-13(21)11-17(12)19/h11,14-16H,1,4-10H2,2-3H3/t14-,15-,16-,19+,20-/m0/s1 | | InChIKey | KQRGETZTRARSMA-DAELLWKTSA-N | | SMILES | C1(=O)C=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)C(=O)CC3)CC2=C |
| | 6-Methyleneandrost-4-ene-3,17-dione Usage And Synthesis |
| Uses | 1,2-Dihydro Exemestane is a related compound of Exemestane (E957000). | | Synthesis | The general procedure for the synthesis of (8R,9S,10R,13S,14S)-10,13-dimethyl-6-methylene-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione from formaldehyde and androstenedione was as follows: 2.0 g of androst-4-ene-3,17 -dione (0.01 mol) was dissolved in 13 mL of anhydrous THF and 2 mL of ethanol, 2 mL of anhydrous triethyl orthoformate and 26 mg of p-toluenesulfonic acid monohydrate were added. The reaction mixture was stirred at 40 °C for about 1 hour. Subsequently, 50 mg of p-toluenesulfonic acid monohydrate was added and stirring was continued for about 2 hours. After the reaction was completed, cooled to room temperature, 1 mL of N-methylaniline and 1 mL of 40% formaldehyde aqueous solution was added to the reaction flask and the mixture was stirred at 40°C for about 4 hours. After cooling to room temperature again, 10 mL of 37% HCl was added and stirring was continued for 2 hours. The reaction solution was transferred to a partition funnel and extracted with EtOAc. The organic phase was dried with Na2SO4 and purified by silica gel chromatography to afford 0.84 g of 6-methylene-androst-4-ene-3,17-dione (3) as a white solid with >95% chemical purity and a melting point of 159-163 °C. | | References | [1] Patent: WO2010/76811, 2010, A2. Location in patent: Page/Page column 9
[2] Steroids, 2013, vol. 78, # 11, p. 1148 - 1151
[3] Patent: CN105622694, 2016, A. Location in patent: Paragraph 0010 |
| | 6-Methyleneandrost-4-ene-3,17-dione Preparation Products And Raw materials |
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